Selective hydrogenation of alkynes to alkenes in the presence of a phosphorus compound and an organic sulphur compound

A compound and selective technology, applied in metal/metal oxide/metal hydroxide catalysts, organic chemistry, compounds of Group 5/15 elements of the periodic table, etc., can solve problems such as difficult separation of compounds

Pending Publication Date: 2021-12-31
DSM IP ASSETS BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Overhydrogenated compounds may be difficult to separate from the desired product

Method used

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  • Selective hydrogenation of alkynes to alkenes in the presence of a phosphorus compound and an organic sulphur compound
  • Selective hydrogenation of alkynes to alkenes in the presence of a phosphorus compound and an organic sulphur compound
  • Selective hydrogenation of alkynes to alkenes in the presence of a phosphorus compound and an organic sulphur compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0178] The present invention is further illustrated by the following experiments.

[0179] List of additives used in the examples:

[0180] AS1 2,2'-(Ethane-1,2-diylbis(sulfanediyl))-bis(ethane-1-ol) AP1 Triphenylphosphine AP2 1,2-Bis(diphenylphosphine)ethane AP3 1,3-Bis(diphenylphosphino)propane ASP Triphenylphosphine sulfur (Ph 3 P=S)

[0181] Selective hydrogenation series 1:

[0182] Hydrogenation of methylbut-3-yn-2-ol to methylbut-3-en-2-ol

[0183] The hydrogenation catalyst (80 mg, palladium-lead on calcium carbonate containing 5% palladium by weight) was placed in a 500 ml pressure reactor. The corresponding additives in the amounts given in Table 1 and a total of 270 g of 2-methylbut-3-yn-2-ol were added to the reactor. The vessel was sealed and purged 3 times with nitrogen (pressurized to 6 bara and released). The reactor was heated to 70°C and purged 3 times with hydrogen (pressurized to 4 bara and rele...

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Abstract

The present invention relates to a process of hydrogenating an alkyne selectively to an alkene by hydrogen using a hydrogenation catalyst which is palladium supported on a carrier in the presence of an additive mixture of an organic phosphorus compound (AP) and an organic sulphur compound (AS).

Description

technical field [0001] The present invention relates to the hydrogenation of alkynes to alkenes. Background technique [0002] Alkynes can be hydrogenated to alkenes by hydrogen gas in the presence of noble metal catalysts. Palladium catalysts can be used to hydrogenate alkynes to alkenes. [0003] An important type of alkyne is an alkyne alcohol while an important type of alkene is an enol. Alkynols or enols, respectively, are substances that are produced on an industrial scale and are of high importance, especially for the fields of vitamins and aroma chemicals. A non-exhaustive list of such important alkynols and enols are 2-methylbut-3-yn-2-ol, 2-methylbut-3-en-2-ol, 3,7-dimethyl Oct-6-en-1-yn-3-ol, 3,7-dimethylocta-1,6-dien-3-ol, 3,7,11,15-tetramethylhexadecan-1 -Alkyn-3-ol and 3,7,11,15-tetramethylhexadec-1-en-3-ol. [0004] Several problems exist in the hydrogenation of alkynes and acetylenic alcohols. One problem is that besides the carbon-carbon triple bond, o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/17C07C33/02C07C33/03
CPCC07C29/17C07C33/03C07C33/02B01J23/44C07C33/025C07C2601/18C07C2601/16B01J27/232B01J35/0013C07C33/14C07C33/16C07C323/12C07F9/50
Inventor 乔纳森·艾伦·米德洛克莉丝·玛丽卡·莫利纳里
Owner DSM IP ASSETS BV
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